Woolford Vacation Packages

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Your Woolford Vacation

Say bye-bye to the stress of planning and hello to a Woolford vacation package. With the finer details organized before you go, you can focus on discovering every inch of this city, starting with Downtown Cambridge, which is good for bars and pubs, culture and cafes. In the mood for a bit of sightseeing? A trip to Woolford wouldn't be complete without checking out Harriet Tubman Underground Railroad National Historical Park, Spocott Windmill and other major attractions. Your ideal Woolford vacation is just clicks away. Search flights, hotels and more on Expedia for a getaway that's tailored just for you.

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Woolford Hotel Deals

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
Woolford
9.8/10 Exceptional! (10 reviews)
Blue Heron
"Plenty of room, well stocked kitchen, great spaces. Kayaks and ping pong big hit. Outdoor spaces was good, although high tide and rain made it swampy. Screened in porch looking out to water a treat."

Reviewed on Jun. 19, 2025

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The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
Solomons Inn Resort & Marina
Solomons Inn Resort & Marina
2.5 out of 5
155 Holiday Dr. P.O. Box 1099, Solomons, MD
Fully refundableReserve now, pay when you stay
The price is CA $196 per night from Jul 13 to Jul 14
CA $196
per night
Jul 13 - Jul 14
7.8/10 Good! (822 reviews)
"Wonderful stay and the king suite was amazing! Pool was big. And breakfast was mostly grab n go but plentiful. We will definitely be back! Staff was very nice!"

Reviewed on Jul. 6, 2025

Solomons Inn Resort & Marina
Hyatt Regency Chesapeake Bay
Hyatt Regency Chesapeake Bay
4 out of 5
100 Heron Blvd, Cambridge, MD
Fully refundableReserve now, pay when you stay
The price is CA $312 per night from Jul 21 to Jul 22
CA $312
per night
Jul 21 - Jul 22
8.6/10 Excellent! (1,003 reviews)
"The Hyatt is a great stay. Balconies outside need painting. Staff and amenities otherwise are great."

Reviewed on Jun. 22, 2025

Hyatt Regency Chesapeake Bay
See all 517 properties in Woolford
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Woolford vacation package cost?
You'll find cheap prices on Expedia for your Woolford break. However, factors like the hotel choice, length of stay and season will influence how much your vacation to Woolford costs.
What are the cheapest months to go to Woolford?
Travel in the shoulder or low season and you're likely to get cheap Woolford vacation packages. Keep in mind that public holidays and major local events can impact prices, so do a little research before booking.
How many days is enough for Woolford?
With a well-organized travel plan, you can easily visit the top Woolford sights in a few days. But if you want to discover hidden gems or take day trips, think about booking your Woolford vacation for longer.
How to find the best Woolford package deals?
Use Expedia's filters to help you find some unbeatable Woolford package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your break for midweek, or browse for Woolford package deals in the low season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it's typically best to lock in your vacation package as soon as possible.
Is it cheaper to book a Woolford vacation as a package?
An Expedia vacation package could score you significant savings when compared to arranging accommodations and flights separately. Better still, you can customize your Woolford trip to fit your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a vacation package to Woolford?
If you've got your Woolford vacation dates finalized, book as soon as you can to grab some terrific deals. With Expedia, you can generally reserve some flights up to a year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are ideal for quick escapes.
How to plan a trip to Woolford?

  1. Choose when to go: Check your schedule and get your bags packed. Your preferred time of year and the type of activities available will also help you decide when to escape to Woolford.
  2. Calculate your budget: Ensure you have enough money to cover everything from transportation and food to experiences and flights. Your accommodations will likely be the largest expense during your trip to Woolford.
  3. Decide how long to go for: Now that you know more about Woolford, you can work out the ideal length of your vacation. Put together a draft plan and allocate enough time to get through everything on your must-do list.
  4. Bundle your hotel and flights: Awesome destination, check. Length of stay, check. Now all that's left is to find a Woolford vacation package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.